3-(5-Allyl-benzothiazol-2-ylmethoxy)-2,6-difluoro-benzamide → 2,6-Difluoro-3-(5-propyl-benzothiazol-2-ylmethoxy)-benzamide

HRID 538517Notes

Reaction equation

[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([CH2:12][O:13][C:14]3[C:15]([F:24])=[C:16]([C:20]([F:23])=[CH:21][CH:22]=3)[C:17]([NH2:19])=[O:18])=[N:9][C:8]=2[CH:25]=1)[CH:2]=[CH2:3]>CO.[Pd]>[F:24][C:15]1[C:14]([O:13][CH2:12][C:10]2[S:11][C:7]3[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:25][C:8]=3[N:9]=2)=[CH:22][CH:21]=[C:20]([F:23])[C:16]=1[C:17]([NH2:19])=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-(5-allyl-benzothiazol-2-ylmethoxy)-2,6-difluoro-benzamide (0.1 g, 0.27 mmol) in 5 ml of anhydrous methanol was added to 20 mg of dry Pd—C. The reaction mixture was stirred at 25° C. for 12 h under hydrogen atmosphere. The reaction mixture was filtered over the celite bed. The filtrate was evaporated to dryness under reduced pressure and the compound was crystallized with ethyl acetate/hexane to give the title compound as light yellow solid (0.014 g, 14%). 1H NMR (DMSO-d6, 400 MHz): δ 0.92 (t, 3H, J=7.2 Hz), 1.62-1.68 (m, 2H), 2.71, 2H, J=7.2 Hz), 5.67 (s, 2H), 7.12 (dt, 1H, J=8.8 Hz (o-coupling) J=1.6 Hz), 7.32 (d, 1H, J=8.4 (o-coupling), 7.38 (dt, 1H, J=9.2 Hz (o-coupling), J=5.2 Hz), 7.83 (s, 1H), 7.89 (broad s, 1H), 8.01 (d, 1H, J=8.4 Hz (o-coupling). 8.17 (broad s, 1H). MS ES+(363.08), HPLC (method 5) Rt=17.64 min.

Workup

filtrationThe reaction mixture was filtered over the celite bed
customThe filtrate was evaporated to dryness under reduced pressure
customthe compound was crystallized with ethyl acetate/hexane

Sources & evidence

ORD record: ord-3fd2635af06c494ca935f13bfeb43946
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865736B2

Reaction notes

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